


Conan O’Brien, Don’t Stop

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF
Genre: Angst, Blow Jobs, Comedy, Conan O’Brien - Freeform, Conan O’Brien Can’t Stop, Cunnilingus, Established Relationship, Explicit Language, Explicit Sexual Content, F/M, Face-Fucking, Face-Sitting, Fluff, Hand Jobs, Legally Prohibited Tour, Long-Term Relationship(s), Oral Sex, Smut, The Legally Prohibited from Being Funny on Television Tour, Vaginal Fingering
Language: English
Status: Completed
Published: 2020-08-10
Updated: 2020-08-24
Packaged: 2021-03-06 07:48:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 13,761
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25819846
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Conan O’Brien sets out on the ‘Legally Prohibited from Being Funny on Television’ Tour, accompanied by his girlfriend, Gwendolyn.
Relationships: Conan O’Brien/Original Female Character
Kudos: 11





	1. 1

**Author's Note:**

> I will add tags as I go along if necessary. Thank you for taking the time to read. If you enjoy the story, please leave a comment or come say hi on tumblr at fandomtransmandom :-)

Foot jiggling in the air as one lanky leg crossed the other, Conan chewed on a toothpick, twirling it in the corner of his mouth.

“Alright, so we’re looking at 42 shows,” Jeff Ross passed out a stack of itineraries to everyone in the circle. “32 cities. US and a few in Canada. Around ten weeks.” Sitting down, he pushed his glasses up his nose. 

Scanning the paper, Conan read the header,  _ Conan O’Brien: Legally Prohibited from Being Funny on Television Tour _ and nodded approvingly. “Good, good.” Gwendolyn appeared at his shoulder with two glasses of red wine, handing him one. “Thanks, hun.” He gave her a peck on the cheek and she scratched the ginger hair under his chin. “So, what’s next?” Conan turned back to Jeff.

”Well,” Jeff leaned forward, folding his hands. “We announce the tour, sell the tickets, and then I guess you just have to figure out what you’re going to do in front of 42 different audiences.” He smiled.

Conan chuckled. “I’ve been tap dancing in front of a crowd like a methed out monkey for 17 years, Jeff. I think I can come up with something to fill the time.” The group laughed and Conan took a drink while Gwendolyn casually stroked the orange tendrils at the back of his neck. Making a few more precursory arrangements, people began trickling out and soon Conan and Gwendolyn had the house to themselves, choosing to sit outside in the early evening air.

“Well,” he began, finishing his wine. “Ten weeks is a long time, I suppose. But we can call. And I’ll see you when we do the shows here in LA. Maybe you can teach me how to do that video chat thing, too.” He nodded, swirling a glass full of nothing.

Gathering her eyebrows, Gwendolyn tipped her head. “You don’t want me to come with you?”

Conan blinked. “You...want to?” They’d only been dating a few months. Brimming with confidence at the time, Conan had run into her backstage while doing press back in September, him there for  _ The Tonight Show _ , Gwendolyn promoting her new book. He got her laughing and they hit it off instantly. When things began to crumble, he hadn’t expected her to stick around. They’d only known each other a short time, after all, and it was an exceptionally public, high pressure situation that Conan himself didn’t want to be going through, much less inflict on anyone else. But Gwendolyn stood by him. Listening to his prolonged rants after every aggravating day, giving him massages to help calm down, patient when he lost his temper over the milk running out, because Gwendolyn knew it was never about the milk. 

But this? Even though they spent practically every night together, they hadn’t moved in, Gwendolyn still had her own apartment. And they’d only gone away together once. It had been Gwendolyn’s idea. About a week after leaving  _ The Tonight Show _ , Conan was dragging himself around the house listlessly when she surprised him with plane tickets. Flitting off to a lovely resort, she insisted on hauling him out of the hotel room and smothering him with sunscreen, pulling him into the ocean after her. Despite himself, Conan ended up having a great time.

Ten weeks, however, of hotel rooms, plane rides, and cramped buses? That could prove...difficult. But in truth Conan would’ve missed her terribly.

“Of course I want to come.” Gwendolyn smiled. “I mean, I may have to skip a couple of shows to fly back for readings or press, but for the most part I should be able to come along the whole way.”

Brushing an errant strand of auburn hair away from her forehead, Conan took her face in both of his large, freckled hands and kissed her, beard bristling around her mouth. 

“Thank you.” Conan pulled back, blue eyes twinkling as he smiled broadly. Nodding, Gwendolyn leaned forward and pressed a kiss to his temple. Heading inside as darkness fell, they went to bed, visions of what the next few months might contain swirling in Conan’s mind.

**

Covering her mouth to smother her laugher, Gwendolyn watched as Conan lay on the floor, surrounded by a plethora of boxes containing half-eaten pizza and wearing a huge fake belly and beard. They were shooting an opener for the live show and Conan was, as usual, being ridiculous. 

Finishing the ‘depressed Conan’ portion of the video, they switched gears to the ‘getting in shape’ montage. Watching him tear off the costume and working out, Gwendolyn had to admit she found him sexy in his gray sweats, even when he was just trying to be silly. Especially then, in fact. They wrapped and she strolled up to him, hanging her hands on the front of his shirt and tipping her face up for a kiss.

“Hey there.” She murmured, meeting his lips briefly before breaking away and looking around the room. “How much longer is, um...everyone going to be here?”

Frowning, Conan rubbed her arm. “Oh, I’m sorry. I know we’ve been in the way all day and it’s been a lot of noise and stuff. It won’t be much longer. Promise.”

“Oh, I’m not bothered by the noise…” Gwendolyn looked him up and down, bringing her body close and making her eyebrows dance.

Conan blinked. “Oh,  _ oh,  _ okay then,” he chuckled, rubbing his hands at her waist. “Let me see what I can do to speed things along.”

But it was another two hours before the cameras and crew members were trailing off and Conan and Gwendolyn could hop back in his car. 

“Whew, sorry,” he turned the ignition and pulled away. “Those things always take twice as long as you expect. 

Gwendolyn curled Conan’s orange hair over his ear. “That’s okay, don’t worry about it.” She continued playing with his hair while he drove, tracing down to his sharp jawline. Then her fingers began tiptoeing down his body, squeezing his slender thigh gently before palming the pouch of his cock through the sweatpants.

“Hey, what’re you doing there?” Conan chuckled, looking to her briefly before returning his eyes to the road. Shrugging, Gwendolyn unbuckled herself, smiling coyly as she bent over the center console, inching Conan’s sweatpants down a little and releasing his cock. Conan just shook his head and smirked as she began stroking him, wrapping her voluptuous lips around the head and whipping her tongue around the sensitive tip until he was fully hard. Sinking down, Gwendolyn buried him in her throat and Conan had to fight to keep his eyes open as she began to bob, hollowing her cheeks, saliva dripping down his thick shaft as she used her wrist to work him in time to her movements.

Conan tasted slightly salty from his sweat, but Gwendolyn didn’t mind. As his desire grew, his hips began to rock forward into her mouth. She loved when he got excited like this, when one of his sizable hands grabbed a fistful of her crimson hair and began pushing her down on his massive cock, fucking her face shamelessly, it made her want to use her free hand to reach in between her own legs. Moaning around his skin, Gwendolyn sped up, Conan’s breath hitching above her.

“ _ Gwen, fuck, don’t stop, _ ” Conan whined, gripping the steering wheel until his knuckles were white, grateful for cruise control. Otherwise he would accidentally have pressed the pedal to the floor by now in the fury of his passion.

Gwendolyn could sense him throbbing against her tongue. “ _ Oh fuck, Gwen, your mouth...I’m gonna cum. _ ” He cried, and Conan dug his fingertips into her scalp, warm cum painting the back of her throat as he struggled to stay in the lane.

Lifting her head, Gwendolyn returned to her seat, buckling back up and wiping her eyes. Conan put himself away and rolled his neck.

“Damn, that was hot.” He rubbed a hand over his scruffy face. 

Leaning back, Gwendolyn pressed a quick kiss to his neck. “You’re welcome.”

Conan slid a hand across to caress one of her creamy thighs, working his way up her skirt as he slowed at a stoplight. Long fingers petting her over the fabric of her panties, Conan grinned at how wet she already was before slipping inside, circling her clit delicately.

Leaning back against the headrest, Gwendolyn let out a melodious sigh. Conan’s dexterous, lengthy fingers knew exactly how to touch her. Teasing and tickling, Conan knew precisely when to apply pressure, when to back off, and with the mere tips of his fingers he could coax her to formerly unknown heights of pleasure.

They were almost back to his house when Gwendolyn began grinding against Conan’s hand, moaning softly and clinging to his arm. Pulling into the garage, he withdrew and they scrambled inside, mouths fusing as soon as they got in the door. 

Conan carried Gwendolyn to the bedroom, tossing her on the bed before peeling off her panties. Laying between her legs, he kissed and nipped at the inside of her thighs before brushing his lips over her slit. Spreading her with his fingers, Conan began lapping at her clit, reveling in the taste of her desire.

Enjoying the chafe of his beard on her thighs, Gwendolyn’s legs shut tightly alongside his head as Conan began sucking on her swollen clit. Two of his extended fingers entered her, stimulating the sensitive patch of tissue with pulsing pressure in sync with his clasped lips until Gwendolyn’s hands were nearly tearing the orange hair from his scalp and she dripped down the whiskers of his beard.

“ _ Conan, fuck, yes, YES! _ ” She cried, body twitching around Conan’s fingers as she quaked, Gwendolyn’s pale skin flushed a bright pink as her last breathless moans fell from her lips.

Emerging, Conan wiped his face on his arm and kissed his way up Gwendolyn’s body, settling beside her on the pillows. Carding her fingers through his hair, Gwendolyn draped a leg over Conan and he rubbed a hand at her waist.

“So,” his tongue darted over his lips. “You’re really sure you want to do this? The tour and everything, I mean? It might be...a lot.”

Smiling, Gwendolyn began to trace his lower lip with her thumb. “Positive.”

**

“Okay, this feels weird.” Conan chuckled as the plastic wrap settled over his head. They began applying the makeup and it wasn’t long before he was looking in the mirror at a bald version of himself. After years of being known for his signature orange pompadour, it was surreal, and he delicately ran a hand over the smooth surface. 

Stepping into the bathroom, Conan changed into the stiff suit costume of ‘The Executive’ and donned the wire glasses. When he walked out, Gwendolyn was entering the room bearing a bag of takeout. She took one look at him and burst out laughing.

“Oh, honey, I’m sorry.” She walked up and scratched his beard. “But you look...well…”

Conan shook his head, smiling. “So is this your way of telling me you’ll leave me if I go bald?” 

Gwendolyn pulled his tie free of the suit, dragging it between her fingers. “No, of course not. Haven’t you noticed by now I’m with you for your money?” Conan chuckled and drawing him close, she leaned in to his ear. “Plus, you have a  _ beautiful _ dick.” Gwendolyn whispered, winking at him.

Conan leaned back and clutched his belly in laughter, face crinkling. “Well, I guess it’s good to know that even if I end up bald and poor, I’ll always have that.”

“Yeah, you couldn’t get rid of me that easily, O’Brien.” Gwendolyn tucked the tie back into his jacket and her emerald eyes looked into his own. “I’m not going anywhere.”

Conan brushed her hair away from her face and gave her a brief kiss just as the director was calling him to the chair. After they wrapped the scene, Sona helped Conan peel away the bald cap and free the wild animal that was his hair, and he sat down to eat cold Thai food with Gwendolyn.

**

Teal Fender Strat slung across his body, Conan picked out a complicated lick while they stood around deciding what song to do next. Gwendolyn watched as they did a riff with ‘On the Road Again’ spinning it to be ‘My Own Show Again.’ Though she obviously found it funny, and she knew there was value in Conan turning his pain into comedy, the underlying sting of it still pained her. There was no doubt in her mind Conan would indeed have his own show again and it would be a resounding success. He had an abundance of avid fans, and a hard-working, kind, talented man like himself would always find success somehow, but witnessing the disrespect he’d faced from some in the interim had been torturous, and seeing that buried hurt bubble up, even in the form of laughter, made her ache.

Polishing up the song and taking notes with Brian Stack, Conan ran it one more time with the group, happy with the result. Going through the rest of the set list, they finished up and Conan flopped down on the couch next to Gwendolyn, balancing his guitar in the corner. 

“Great job today,” Gwendolyn rubbed his arm.

Smiling, Conan pecked her cheek. “Thanks, hun. It’s really starting to come together. We’re auditioning the back-up singers tomorrow.” He leaned in and pressed his forehead to hers. “Though you could save us some time and be one of them…”

Gwendolyn pushed him away playfully. “Don’t be silly.”

“Aw, come on.” Conan pinched her hip and Gwendolyn squealed. “Don’t think I haven’t heard you singing in the shower. You’re pretty good.”

Pressing a hand to her forehead, Gwendolyn sighed. “Oh jeez, remind me never to do that again. No,” she grinned at him. “You’re the rockstar, not me. I’ll stick to writing, thanks. Plus,” Gwendolyn shook her head in horror. “I wouldn’t get on a stage in front of all those people if you paid me.”

Conan chuckled. “Ah, right. Stage fright. I forgot.”

“It really doesn’t scare you? Being out there in front of all of those people?” She tilted her head.

Conan frowned appraisingly. “Well, it does. But not in the same way as for you I don’t think.” He shook his head. “I don’t worry so much about failing, you know, making a fool of myself. Not anymore, at least. After all, that’s kind of my job.” Conan grinned. “But I do worry about disappointing people. I worry that they’ll come to see me, expecting something, and I won’t be able to deliver. That they’ll leave feeling cheated.” He shrugged, mouth settling into a flat line.

“Oh, honey,” Gwendolyn rubbed his shoulder. “You’re going to be amazing. Seriously, after what I saw today? People are going to walk away awe-struck. Trust me, you have nothing to worry about.” 

Turning to her with a half smile, Conan nodded. “Thanks, Gwen. I hope so.” 

**

Having announced the dates (which sold out with such haste it gave Conan intense anxiety) cast his back-up singers, and managing to piece together something he hoped would make for an entertaining show, Conan paced as they prepared for the Invited-Audience Dress Rehearsal. Sure, it was mostly comprised of his staff, but he was still hoping to find out which bits and songs would float and what would crash.

Gwendolyn saw Conan striding back and forth, pausing every few laps to let a toe tap rapidly against the floor for a few seconds before resuming his circuit. 

Approaching him, she tugged on his blue button-up. “Hey, how are you doing?”

Glancing at her, Conan gave a brief smile before his eyes began to roam once more around the crew, the stage, and the set up. “Hey. Fine. I’m fine.”

“Conan,” Gwendolyn took his face in her hands, turning him toward her. “How  _ are _ you?”

His cerulean eyes met Gwendolyn’s and Conan sighed, seeming to physically deflate. “I’m...nervous. I mean, I know everyone out there and all,” he gestured vaguely in the direction of the crowd. “But it feels like there’s a lot riding on this anyway. And at the same time,” Conan rubbed his forehead. “I have no fucking idea if we’re going to get a genuine response to anything, because maybe everyone in that audience is just going to kiss my ass.” He threw up his hands in exasperation.

“Conan,” Gwendolyn brushed back the sides of his coiffed orange hair so as not to mess it up. “You’re going to be wonderful. You got this.” Smiling briefly, Conan began chewing his lip and fiddling with his fingers against his thigh, once again glancing at the stage where they were continuing to put things together.

Gwendolyn narrowed her eyes. “Hey, how much time do you have before you have to be out there?”

“Um…” Conan shook back his sleeve and checked his watch. “Just over half an hour. Why?”

Crooking her finger, Gwendolyn got Conan to lean down and whispered into his ear. “Wanna go fool around in your dressing room? Might help you rel-“

“Yes. Let’s go. Now.” Nodding eagerly, one of Conan’s wide freckled hands grabbed her upper arm and led her forcefully down the hallway. Even at his normal pace Gwendolyn struggled to keep up with his long-legged stride, but the gait of an excited Conan practically forced her to jog. Peeking in the room, Conan was grateful that neither Sona nor anyone else was inside and he dragged Gwendolyn through the door, locking it behind them and pushing her up against the wall. 

Mouths meeting, Conan’s hand crawled under her shirt, snatching down the front of Gwendolyn’s bra and caressing a breast while the other fisted itself in her mass of crimson hair.

“Get your fucking panties off.” He breathed against her lips, and Gwendolyn shimmied them down her hips, kicking them aside when they reached her heels. Walking them backwards to the couch, Conan barely managed to dodge the coffee table, falling back, and Gwendolyn straddled him. 

Unbuckling and unzipping his pants with record speed, Conan lifted his erection from his boxers. Gwendolyn placed a hand between them to position him at her entrance and sank down immediately, head falling back and emitting a deep groan as she stretched to accommodate his thick cock. Snatching her by the back of the neck, Conan claimed her mouth once more, kissing her breathlessly as Gwendolyn began to bounce and grind, one of Conan’s thumbs rubbing frantically over her clit. 

“ _ Oh yeah, oh fuck.” _ Leaning back, Conan clamped his free hand onto her hip and rocked up into her, panting hard as her hands slid over his chest. Gwendolyn brought her face to his neck, his beard scratching her as she curved her body to drive him deeper, desperate moans echoing against his ear. Dragging her hips forward faster, Conan laid his head against hers, chest heaving as her body fluttered around him.

“ _ Conan, fuck, yes! _ ” Gwendolyn clung to him, thighs trembling and breath hot and wet on the skin of his neck. The pressure around his cock was overwhelming, and muffling his cry by pushing his face into her tumbling hair, Conan shuddered forth, long arms drawing her near, inhaling her sweet scent as they rocked together.

Giving a languid kiss first, Gwendolyn climbed off and Conan put himself back together. He was slightly rumpled now, but found he wasn’t as worried about it as he might’ve been. They got up and Gwendolyn retrieved her panties from the floor, inching them back up under her skirt. Checking in the mirror and making several minuscule adjustments, Conan looked to Gwendolyn, who nodded in approval, and they proceeded back toward the stage.

The show went relatively smoothly. A couple of sound hiccups that Conan was easily able to plaster over with jokes, one song that got a slightly lukewarm reception, but otherwise it was great. Exhilarating, even. Conan had always secretly wanted to spend more time performing musically, but despite encouragement from Gwendolyn and others, he didn’t think he truly had the talent to carry it off without making at least half a joke out of it. But being able to play with the band in front of a crowd, fingers dancing up and down the neck of his guitar, rhythm rolling over his skin, bass pounding through his very bones; it was surreal.

And when he walked off the stage, it was as if any nerves he’d felt before the show had been recycled into manic energy. Spotting Gwendolyn, Conan jogged to meet her, taking her face in both hands and kissing her in the middle of the crew. Eyes open, she looked around, caught off guard and a little sheepish when he pulled away.

“Alright, everybody.” Conan clapped his hands together, beaming. “Let’s go celebrate. Come on!” People whooped and hollered. Hitting a local bar, the group grew raucous fast, Conan performing bits for everyone’s amusement, and Sona laughing so hard she was crying. 

Calling a car to take them back home, Conan and Gwendolyn peaceably held hands in the backseat, reflecting on the night.

“So I’d say that was a success.” She grinned, blinking Conan into focus. Gwendolyn rarely imbibed, so even with only three drinks she was buzzing.

Nodding, Conan rubbed circles into her palm with his thumb. “Yeah. Better than I expected.” Lifting her hand to his lips, he gave it a whiskery kiss. “Thank you for being there.”

Gwendolyn squeezed his hand. “Of course.” The rest of the ride passed in companionable silence and when they got back to Conan’s house they tumbled into bed, tipsy and satisfied.

  
  



	2. 2

Touching down in Eugene, Oregon they disembarked from the plane and Conan held out his hands to a crowd of no one. “Alright, everybody back! We need some room, here! Back, I say!” Gwendolyn laughed, ruffling his orange hair as they piled into the car and made their way to the hotel. 

As per usual, Conan was approached by fans as soon as people recognized his lanky form. “Hey man, love your work. You got a real raw deal, bud.” A burly man in a trucker’s hat said as he took Conan’s hand in both of his meaty paws.

“Thanks, man. I appreciate it.” Conan smiled, but Gwendolyn could sense the underlying current of sadness that rose to the shore every time a stranger felt the need to comb over the events of the past few months. She knew people wanted to express support, that intentions were good and they were just trying to be kind, but Gwendolyn still wished it didn’t come up everywhere they went.

Dropping their things in the hotel room, Conan rolled his neck and fell like a starfish back on the bed, his long limbs extending well past its boundaries. Gwendolyn climbed on top of him, straddling Conan’s slender hips. 

“So,” she leaned forward, crossing her arms over his chest and resting her chin on top. “How are you feeling about the first show?”

Conan jiggled her ass, sighing. “Decent, I suppose. I mean, nervous. But we’re as prepared as we’re going to get.”

Nodding, Gwendolyn tilted her head and brushed back his hair. “You’re going to be great.”

“You think so?”

Tipping forward, she met Conan’s thin lips. “I know so.” 

***

Sitting in front of the mirror, Conan kept turning his face and Gwendolyn was getting frustrated.

“You need to hold _still._ ” She poised the brush over Conan’s prominent cheekbone.

Conan frowned. “You’re going to put on too much.”

“I am _not_.” Gwendolyn sighed. “Now will you quit bitching and let me do this? I’ve been wearing makeup practically my whole life.”

Raising an eyebrow, Conan tried to speak without moving his mouth too much. “Well, I’ve been wearing it for 17 years, so I think that should count for something.” Gwendolyn bopped him on the nose with the butt end of the brush and he pinched her in retaliation.

“Okay, now the highlighter.” Swirling a fresh brush around in a new compact, it slid over his face. As much as Conan disliked the weight of makeup on his skin, this part he kind of enjoyed, the way the tools moved over him was soothing. And having Gwendolyn do it, her face narrowed at him in concentration as she delicately applied the various products, not bothering to hide the fact that he used the angle to look down her dress, was a welcome change.

“There. Done.” Taking a step back to admire her work, Gwendolyn grinned. 

Peering at his reflection, Conan nodded. “Well, I _suppose_ that’ll do.” Playfully hitting his shoulder, Gwendolyn walked to the coffee table and cracked open a bottle of water.

”Okay, everybody out,” Conan called to the room, unzipping his hoodie. “Gotta change.” Sona, Andy, and the others left but Gwendolyn remained behind as Conan pulled his t-shirt over his head, tossing it aside before unzipping his jeans and pushing them down. Watching, Gwendolyn saw his boxers hanging low on his lithe body, a tuft of orange hair peeking out of the top.

“Hey, come over here.” Gwendolyn bit her lip, smiling coyly.

Unzipping his garment bag, Conan barely looked in her direction. “Hmm? What’s that?”

“I said,” she tapped her fingernails on the coffee table. “Come _over_ here.”

Finally glancing up, Conan caught the twinkle in Gwendolyn’s eye and a grin broke across his face. “Oh, alright then.” Raising an eyebrow, he replaced the hanger and strode over to her in his boxers. 

Once he was in range, Gwendolyn took Conan’s narrow hips in hand, pulling his waistband down until she exposed his soft cock. Holding his gaze, she took the head into her mouth, sucking gently and humming in pleasure. Conan grew stiff in her mouth, and as she slowly took him deeper he wound his freckled hands into her scarlet hair. Often Gwendolyn would use her hands while she sucked him, but today they stayed firmly at his waist, guiding him, she used the muscles of her throat and the pressure of her tongue to stimulate Conan until he had to put a hand over his own mouth to stifle the moans. Desperate for release, Conan rocked into her face, knees threatening to buckle.

“ _Fuck, Gwen, I’m gonna cum._ ” He gasped, removing the hand from his mouth, and falling forward, Conan gripped the back of the couch for balance as he arched over her, Gwendolyn swallowing eagerly as his cock throbbed against her tongue.

Sitting back, Gwendolyn wiped her face and Conan had to sit for a minute, lifting his boxers and collapsing beside her on the couch.

“Fuck.” Conan dragged his hands down his face before hooking a hand around her neck and pulling her near to kiss her temple. “Thank you, honey. I really needed that.”

Nuzzling into his neck, Gwendolyn trailed her fingers over his orange chest hair. “Anytime.You know how much I love sucking that cock of yours.” She nipped playfully at his ear before pressing kisses down his neck.

“Hey now, “ Conan chuckled, cupping her face. “As much as I would _love_ to, I do actually have 2,500 people who paid to see me waiting out there, and somehow I don’t imagine they’ll think me fucking you senseless is a good enough reason for delaying the show.” He smirked, threading a piece of hair behind her ear.

Gwendolyn sighed, smiling. “What a shame.”

Conan finished getting ready and they made their way to the stage. Announcing his name, Conan shook out his hands and Gwendolyn gave him a brief peck.

“You’re going to be great.” She scratched his beard affectionately and Conan nodded, striding out with a wave to the roaring crowd. Gwendolyn watched from the wings as Conan performed; playing, singing, dancing, and generally making a fool of himself as he was wont to do. Beaming, Gwendolyn looked on as Conan coaxed the crowd into a frenzy, everyone standing and clapping exuberantly for her beautiful, talented man. Gwendolyn knew he’d ached for this. Not just over the last months when there was no audience to laugh each night, but his entire life. Conan had nursed dreams of tours and being an old-school vaudevillian since childhood, and to see him going full-throttle, lights flashing and music pounding beneath her feet, made Gwendolyn’s heart swell with pride.

Show coming to a close, Conan stepped off stage and Gwendolyn handed him a bottle of water, which he promptly consumed like a snake unhinging its jaw, making it disappear almost instantly. Once everything was wrapped up, the group insisted once again on stepping out to see what Eugene had to offer. The answer: not much, but they had a fantastic time at a grungy dive bar just the same, boisterous laughter and bawdy humor echoing off the dingy walls.

Aware they all had to be on the plane early to make it up to Vancouver, no one seemed overly concerned as 2 a.m. rolled around and the bar lights flashed, indicating closing time. Swaying on the sidewalk, Conan held Gwendolyn from behind, arms wrapped around her waist, though when he saw most of the others were distracted by a joke, he dove in to kiss her neck, one sizable hand squeezing her ass. In fact, he’d been almost recklessly affectionate all night, fingers tiptoeing across her thigh under the table and making it inches from her panties before Gwendolyn stilled his wrist and gave him a subtle shake of her head.

Kneading her leg on the way to the hotel, Conan took her hand and they walked through the lobby, stumbling a bit. Getting on the elevator, Conan stood beside her quietly, hands folded in front of him. Then the doors closed.

Slamming her against the wall, it was as if Gwendolyn had been hit by a hurricane, Conan’s mouth mashing into hers, hands groping, separating her thighs with a knee and shoving his hips between her legs. 

“Conan, _Conan!_ ” Gwendolyn breathed when she managed to get her mouth free. “What if there’s a camera?”

Shaking his head, Conan caught her lips again “I don’t give a shit.” Dinging for their floor, the silver doors slid open and thankfully no one was standing on the other side as they rushed into the hall. Jerking Gwendolyn back by the arm, Conan hoisted her into the air, and she shrieked, surely annoying their neighbors as he carried her. Worried he might cause them both to tumble in his inebriated state, Gwendolyn held tightly to Conan’s neck as they approached the door, where he had to set her down anyway because he couldn’t extract the key card while keeping her aloft. 

Giggling and shutting the door behind them, Gwendolyn fell back on the bed, kicking off her shoes and Conan removed his hoodie and jeans, tripping on a pant leg and nearly ending up on the floor, both of them laughing uproariously. Pulling her dress overhead, Gwendolyn let it flutter away, struggling for a moment with her bra clasp before managing to free herself. Eventually naked, Conan rolled on top of her, their uncoordinated tongues sliding in and around each other’s mouths as they continued to make each other chuckle, Conan caressing her breasts and grinding his half hard cock between her legs.

Hand creeping between her thighs, Gwendolyn grew wet under his ministrations and soon the laughter died away, replaced with hitching breath and gentle moans.

“You want me to go down on you?” Conan asked, kissing along her neck.

Gwendolyn fought to brush her lips over his face. “Yes, yes, please. Fuck.”

“Yeah, you love it, don’t you?” Biting her neck, Conan’s fingers sped up around her swollen clit. “You love when I lick you until you’re screaming my name.”

Nodding, Gwendolyn’s pelvis seemed to move into his hand of its own volition. “Yes, fuck. Conan, I love it. _I love it._ ”

Dropping between her thighs, Conan dove forth unceremoniously, mouth moaning against her sensitive flesh as he lapped. Gwendolyn gripped his head tight between her legs, voice erupting from her throat at progressively higher pitches as she shamelessly humped Conan’s face.

“ _Conan, yes! Fuck, don’t stop!_ ” Lips fused over her clit, Conan couldn’t help but take his turgid cock in hand and start tugging wildly, the sounds dripping from Gwendolyn were making him ache with desire. Convulsing, Gwendolyn’s legs clamped against the side of his head as Conan heard her scream and go silent, nails grazing his scalp. 

Unable to wait any longer, Conan pushed himself up the bed, lowering his face near Gwendolyn’s and smearing the head of his cock over her entrance.

”I wanna fuck you. _Please,_ I wanna fuck you so badly.” Nodding, Gwendolyn brought two lethargic arms around his neck and Conan sheathed himself to the hilt, groaning as he began pounding into her until the headboard shook against the wall and the neighbors were knocking, yelling for them to be quiet. Too far gone to stop, Conan rubbed a thumb hurriedly over Gwendolyn’s clit, feeling the threat of her orgasm approach as she fluttered around his cock. Scratching his back, Gwendolyn screamed his name, whites of her eyes all that was visible as her body quivered. 

“ _Oh fuck, Gwen._ ” Body clenching him intensely, Conan was unable to hold himself up anymore, collapsing on top of her, hips digging forward while he whimpered and the rest of his body lay limp. 

Attempting to compose himself, Conan could feel the gentle pulses of Gwendolyn’s aftershocks as he remained inside her. Rolling off, he glanced at the clock. They had just over three hours before they had to wake up and get on the plane, making their way to Vancouver. Double checking that an alarm was set, Conan and Gwendolyn fell asleep sprawled across the bed; naked, messy, and satisfied.

***

The first show in Seattle happened to coincide with Conan’s birthday. He was never big into celebrating himself, and the fact that 60 Minutes felt the need to throw him a very public, very fake party, was making him uncomfortable. Conan plastered a smile on his face, though, and did the interview, ate a piece of cake, and took as many pictures as were required of him.

Later, alone in the hotel room, Gwendolyn approached him and tugged on the front of his faded Guinness shirt. “You ready for your present?”

Conan slid his hands down to grab her ass. “ _Yes._ ”

Gwendolyn playfully smacked his shoulder. “No, an _actual_ present, you goof.” Rummaging in her suitcase, Gwendolyn unearthed a rectangular package in shiny purple paper, which Conan promptly ripped open to reveal a first edition of Flannery O’Connor’s _Wise Blood._

“Oh _wow,_ honey, this is great!” Conan ran his fingers over the cover lovingly.

Shaking her head, Gwendolyn smiled. “Look inside.”

Conan did so and saw that somehow, she’d managed to locate a signed copy. He was silent for a while as he stared down at it. “That’s…” he cleared his throat. “Gwen, it’s...it’s perfect. Thank you.” Taking her in his arms, Conan kissed Gwendolyn’s forehead and they stood in the empty hotel room, swaying gently back and forth.

By the time their second show in Seattle rolled around, everyone had learned the error of partying after each show, and they tended to take it easy, having subdued flights between cities at night or amiable bus rides filled with endless joking around. Gwendolyn, however, noticed that though they were no longer drinking, Conan had picked up some bad habits. The manic energy he acquired onstage now seemed to radiate from him constantly, body moving every moment, motivated to double and triple check every step of the process, never willing to say no to any request made of him. 

Standing by, Gwendolyn would watch as hour after hour passed of meet and greets, press interviews, schmoozing big wigs, and Conan generally being “on” at all times. From the sidelines she was exhausted on his behalf, and this was only their sixth show. 

Approaching Sona that afternoon when Conan passed by with Andy, talking excitedly, Gwendolyn lowered her voice. “Hey Sona,” she leaned in. “Do you know when Conan last ate today?”

“You know…” Sona looked off to the side, blinking. “I don’t, actually. He didn’t ask me to order him any lunch.” Nodding, Gwendolyn frowned.

She discovered Conan sitting in a circle with Andy, Sweeney, and Jimmy; foot jiggling uncontrollably while he peered over a stack of papers. “Alright, I’ll get these over to Jeff.” Hopping up, Conan smiled at her, but Gwendolyn reached out to grab his arm.

“Conan…”

“Hey hun, what’s up?” He folded his lip under, fingers fiddling at his side.

Gwendolyn leaned in a little. “When did you last eat?”

Blinking in confusion, Conan shrugged. “I dunno, breakfast? Why?”

“Honey…” Gwendolyn shook her head in exasperation. “It’s almost four. You have to eat something. Come on, sit down.” She attempted to guide him to a table in the corner, but Conan just gathered his eyebrows and held firm.

“I’m not hungry. Plus, I have to take these to Jeff.” He gestured with the papers in his hand.”

“Conan.” Green eyes piercing his own, Gwendolyn squared her shoulders and stared at him intensely. “You. Need. To. Eat.”

Clenching his jaw, Conan’s eyes slid to the others in the room, then lowering his voice, he glared at her. “Don’t talk to me like I’m a child, Gwen…”

“Take care of yourself like an adult, and I won’t have to, Conan.” Her nose flared and Gwendolyn’s fists bunched at her sides. Conan had half a foot on her, but he knew her well enough to see that Gwendolyn was not going to back down.

Conan sighed. “Fine.” He spoke through gritted teeth, hurling himself into the chair. 

“Good.” Gwendolyn narrowed her eyes. “Now, they have sandwiches in the hall. Turkey, ham, or chicken salad?”

Crossing his arms like a surly toddler, Conan looked away from her and muttered. “Chicken salad.”

“Okay then. I’ll get you some fruit, too.” Conan didn’t watch as Gwendolyn left the room, and when she returned she set a plate in front of him. Biting into his sandwich, he chewed resentfully, but halfway through his body realized how voraciously hungry he was and Conan found himself inhaling the rest. Gwendolyn approached him, hands resting on his shoulders and she began to massage. He had no idea how tense he was until the balls of her thumbs were melting into his wire-tight muscles, teasing them apart as Conan finished his meal.

Uncomfortable, the others had casually made their way out of the room during the proceedings, and once Conan brushed the crumbs from his beard, he turned around and held Gwendolyn around the waist.

“I’m sorry,” he murmured into the fabric of her blouse.

Cradling his head, Gwendolyn brushed back his orange hair. “It’s okay. I just want you to be taken care of.”

Conan pulled her down onto his lap, and Gwendolyn tucked her head into the crook of his neck. “You take such good care of me.”

“I think we take good care of each other.” Gwendolyn pressed a kiss to his cheek. 

Arms around her, Conan rocked Gwendolyn lightly. “Hey Gwen?”

“Yeah?”

Silent, Conan bit his lip, swallowing hard. “I’m in love with you.”

Conan felt her tense up in his arms, and for a moment panic soaked down to his bones. Gwendolyn pulled back, studying his earnest blue eyes. “Really?”

Looking back at her, Conan nodded. “Yes.”

Gwendolyn cupped his face, beaming. “I’m in love with you, too, Conan.” 

Their mouths met, but Conan and Gwendolyn found it difficult to keep their lips together, smiles obscuring their kisses. 


	3. 3

Walking into her apartment, Gwendolyn was struck by how strange it smelled. Not bad, just foreign after being away for a while. After doing the Los Angeles shows at the Gibson, she stayed behind while Conan and the crew moved on to Phoenix because she had to do a reading at a local bookstore, and would be flying out to hook up with them in Vegas tomorrow.

Changing into pajamas, Gwendolyn crawled into bed and was just starting the second chapter of a murder mystery when her phone buzzed.

Conan:  _ Hey babe, How did the reading go?  _

__ Smiling, Gwendolyn’s thumbs flew over the keyboard.

Gwendolyn:  _ It went well, nothing too exciting. In bed now, missing you. How are you feeling about the show tonight? _

__ Conan:  _ Oh, pretty good. Still at the hotel. We’ll head to the Dodge in a couple of hours.  _

__ Gwendolyn:  _ Sounds good. I’m sure you’ll have a great show. _

__ Conan:  _ Thanks, hun. What are you wearing? _

Laughing to herself, Gwendolyn shook her head as she responded.

Gwendolyn:  _ That bleach-stained 96 Olympics shirt. Super sexy, ha. You? _

Conan:  _ Nothing. Just got out of the shower. Are you free to call? _

Gwendolyn:  _ Sure. _

Phone vibrating in her hand, she answered and rolled over. “Hey there.” She grinned, scooting into a more comfortable position on the bed.

“Why hello there.” Conan’s voice was deeper, sexier than usual, and it made Gwendolyn tingle. “How are you doing?”

Smirking, Gwendolyn pushed back her hair. “Oh, I’m doing just fine. Wishing you were here with me though.”

“Oh yeah?” She could hear him breathing. “What would we be doing?”

Chuckling lightly, Gwendolyn bit her lip. “Well, you know how much I like it when you’re on top of me. Kissing me, your big hands touching me everywhere.”

“Mmm, yeah, baby, I love the way you feel.” Conan hummed. “You want me to put my fingers between your legs?”

Sliding her hand beneath the waistband of her panties, Gwendolyn closed her eyes. “Yes Conan, yes. Please touch me. You feel so good.”

“Mmm, yeah. Are you wet for me?”

Gwendolyn nodded. “Fuck yes, Conan. You get me so fucking wet. You make me so hot.”

A throaty chuckle came over the line that made all the hair on the back of Gwendolyn’s neck stand up. “Fuck yeah, I love playing with your clit, getting you all excited and making you moan.”

“Conan, let me...let me touch your cock.”

“You want to touch it?” He asked teasingly.

Gwendolyn adjusted the phone against her ear, other hand starting to move quickly in her own slickness. “Yes, please, I miss your beautiful cock. Let me stroke you.”

“Fuck, you feel so good Gwen.” Conan panted.

“Yeah?” She breathed. “You want me to use my mouth instead? You want me to suck your big cock, Conan?”

“Fuck, yes, honey,  _ please. _ ” A high note slipped into Conan’s voice. “Let me feel your throat. I miss it so much.”

Humming, Gwendolyn rubbed her clit harder. “Mmm, yeah. I want you to take that thick cock and shove it all the way down my throat Conan. Fuck my face until I’m drooling and I can hardly breathe.”

“Oh  _ fuck. _ ” Conan’s moans were turning to whimpers, “Wait...wait.” 

“What?” Gwendolyn panted, hand stilling in frustration. “What’s wrong?”

She could hear Conan trying to catch a breath. “Nothing, I just...I just want to fuck you. Let me fuck you, Gwen.”

”Oh yeah, fuck me Conan.  _ Fuck me. _ ” Fingers working double time, Gwendolyn rocked against her own hand. “I want your big cock inside me.”

“Yeah, you like that? You like the way I fuck you?”

Legs twitching, Gwendolyn fought to hold onto the phone.  _ “I love it, Conan. I love it! Don’t stop! Fuck me! Fuck me! _ ”

“Fuck, yeah, Gwen. Cum for me.  _ Cum for me. _ ”

Writhing up and down on the bed and calling Conan’s name, Gwendolyn held her hand still between her thighs as she came down. 

Retrieving the phone from where she inadvertently dropped it on the pillow during her passion, Gwendolyn did her best to steady her voice.

“Did you cum yet?”

Conan’s breath was ragged. “No, not yet, honey.”

“Put that cock in my mouth, then.” Gwendolyn purred.

“Mmm, fuck yes.”

Lowering her voice, Gwendolyn made it as sultry as possible. “I’m sucking you deep. My mouth is warm and wet. And you can thrust into my face as hard as you want.”

“ _ Oh Gwen, oh yeah...your mouth… _ ” Lovely high whines trickled from Conan’s lips as she continued.

“You gonna cum for me, Conan? You gonna cum in the back of my throat? I wanna taste your cum so badly. I want your big cock all the way down my throat and I want your cum all over my long, pink tongue.”

“ _ Oh fuck, fuck, FUCK! _ ” With a shuddering moan Gwendolyn knew Conan tumbled over the edge, and she listened as he gulped air and composed himself.

“Mmm…” he piped up after a couple of minutes. “Can’t wait for the real thing tomorrow.”

“Me neither.” Gwendolyn smiled, shifting onto her side.”

“What time does your flight get in?”

“Um…” she rifled in the bedside drawer and looked at her ticket. “Should be around six. I’ll probably drop my stuff at the hotel and make it to the Pearl not long before showtime.”

Conan sighed in relief. “Great, I’ll see you then. Love you.”

Hearing him say the words still made Gwendolyn giddy. “Love you, too.” They said goodbye and she climbed under the covers, excited to rejoin the tour.

Touching down in Vegas, Gwendolyn moved uncomfortably between her fellow passengers. She’d been spoiled by Conan’s private plane and wasn’t accustomed to the crowded conditions of flying coach, so when they deboarded she felt like she could breathe for the first time in hours.

Discarding her luggage at the hotel. Gwendolyn arrived at the Pearl Theater with about an hour before the show was to start and found Conan applying the finishing touches on his makeup, Sona scrolling through her phone on the couch.

“Hey hun.” He jumped up and gave her a kiss, wrapping her in his lanky arms. “How was your flight?”

Gwendolyn hummed appreciatively at the pressure of his body around her. “Oh, it was fine. Not bad coming from LA. How are things going here?” She glanced around the room.

Conan shrugged. “Oh, not too bad I suppose.”

Just then there was a knock at the door and Andy poked his apple-cheeked face inside. “Hey guys, how’s it going?” His voice sounded clogged and his eyes looked watery.

“Oh no, Andy, are you sick?” Gwendolyn tilted her head in concern.

Rolling his eyes, Andy nodded and came in to sit on the couch. “Yeah. Nothing too serious, but it’s annoying enough.”

“You want me to run out and get you anything?” Gwendolyn offered.

Andy waved a hand. “No, but thank you. I’m already on enough Sudafed that I’m going to be having my own personal Woodstock soon.” They chuckled and Andy wiped his nose with a tissue. After chatting for a few minutes, Conan kicked everyone out so he could change. But as soon as the door closed, Conan locked it behind them, hands crawling over Gwendolyn’s waist.

“Hey.” He bit his lower lip, dragging her close. Gwendolyn giggled as he dipped down to kiss her neck, beard tickling her. Large palm caressing her breast, Conan’s whiskery lips moved against her ear. “Would you suck me, honey? Please?  _ Please?  _ I missed you so much.” Gwendolyn could feel the beginnings of his erection against her hip and the neediness in Conan’s voice made her throb internally with desire. 

“Yeah, come on.” She guided him to the couch and pushed the coffee table out of the way, grabbing one of the throw pillows for her knees while Conan undid his jeans and worked them down his hips, exposing his massive cock. 

Knowing they were pressed for time, Gwendolyn sank down to the root immediately, undulating her throat around Conan’s flesh and pressing her tongue firmly on the underside while rolling his balls between her fingers.

“ _ Oh Gwen, that’s...that’s… _ ” but Conan couldn’t form a sentence as Gwendolyn bobbed hastily, hand working double time on the shaft as Conan’s hips thrusted up to meet her, lengthy fingers digging into her scalp. Gritting his teeth and exhaling moans through his nose, Conan almost rose bodily from the couch as he fucked her face, burrowing into her throat with every stroke. 

“ _ Fuck, Gwen, you’re gonna make me cum! _ ” His feet twisted on the floor and his back arched as something between a cry and a groan burst out of Conan before he fell back on the couch, limp. Swallowing, Gwendolyn rose to her feet and replaced the throw pillow before wiping her face. After zipping up his pants, Conan brought her in for a kiss.

“Thank you, hun. I needed that.”

Gwendolyn pushed back an errant strand of orange hair. “No problem.”

And as it turned out, Conan truly did need it. The first Vegas show was...rocky. Afterward the crew discussed the possibility that much of the audience had likely been comped guests of the casino. There was just a flatness about them compared to the other shows. It seemed to Conan that no matter what he did, what bit, what song, what crazy dance; he couldn’t get the energy up, couldn’t get these people out of their seats. Walking off stage dejected, Conan was quiet most of the way back to the hotel, and when they crawled into bed together and Gwendolyn began kissing his neck, his freckled fingers found her wrist.

“Hey, um...do you mind if we just go to sleep? I’m sorry, I’m just exhausted from the show.”

“Oh, of course, honey.” Gwendolyn rubbed his cheek. “No problem.” Turning over, she tucked herself into Conan’s body and within a few minutes they both began to drift.

Despite Conan’s apprehensions, the second Vegas show went much better. But he was straining himself due to residual nerves from the previous night, ramping up the manic energy, running up and down the aisles, and hurling his body around until Conan’s shirt clung to his back with sweat. 

Downing two bottles of water when he got off stage, Conan coasted on the high, arm around Gwendolyn and laughing with the crew for about twenty minutes before all the adrenaline seemed to leak out of him and his legs turned to jelly. Swaying slightly, he blinked and swallowed, looking around.

Feeling Conan move against her, Gwendolyn eyed him with concern. “Conan...Conan, are you okay?”

“Yeah, yeah.” He nodded. “I think I need to lay down though.”

Rubbing his chest, Gwendolyn guided him to a nearby chair where he sat and covered his face. She knelt down next to him, holding his free hand. “Do you think you can make it back to the hotel, or do you want to go lay in the dressing room?”

Conan took a couple of deep breaths. “Let’s just go back to the hotel. I’ll be okay.” Extending a hand, Gwendolyn helped him up and Conan was especially grateful they’d changed the meet and greets to before the shows instead of after, the thought of facing a sea of fans, signing autographs and taking pictures for the next few hours, made him nauseous as he folded his long body into the car.

Once inside their hotel room. Gwendolyn helped Conan get undressed. 

“Fuck, I really have to take a shower.” He dragged a hand over his weary face.

Patting his shoulder, Gwendolyn led him to the bathroom. “Come on then.” Turning on the water, she shed her clothes and they stepped inside. Conan rested his head on the wall, the cool tile refreshing on his face, while Gwendolyn lightly scrubbed his body. Standing there, her delicate ministrations were soothing, and had Conan not been forced to keep himself upright, he would’ve fallen asleep. 

“Okay, come here.” Gwendolyn intoned softly, hands full of shampoo as she directed him to turn away from her. Fingers massaging his scalp, Conan purred as the suds grew in his orange hair. After, he stood under the stream to rinse himself before climbing out and toweling off, Gwendolyn following. They climbed into bed, naked and clean, and Conan was asleep almost the instant his head hit the pillow.

Waking to the sound of the door clicking shut, Conan looked around blearily with one eye.

“Oh, sorry, hun. I didn’t want to disturb you.” Bringing her into focus, Conan saw Gwendolyn carrying two paper plates loaded with food from the continental breakfast. “I got you a few things if you’re hungry.”

Nodding, Conan got up and pulled on a fresh pair of boxers before joining her at the little table. After his third bite of eggs his body realized he was incredibly hungry, and Conan found himself inhaling the rest. “Mmm, thank you for breakfast.” He said around a mouthful of sausage.

Gwendolyn smiled and squeezed his lithe thigh. “You’re welcome.” After they finished and she threw their plates away, Gwendolyn sat in his lap. “Mmm...a day off.” She grinned, brushing a kiss to his lips.

Conan closed his eyes. “Thank. Goodness.” He let out a deep breath and Gwendolyn combed her fingers through his hair.

“And I’m going to make sure you  _ actually _ take the day off, mister. You’re not getting out of that bed, you hear me?” She wagged a finger in front of his face in mock threat.

Chuckling, Conan’s hands traveled to her ass, squeezing a little. “No complaints here.” Joining their mouths, Conan carried her to the bed before peeling off her clothes and wiggling out of his boxers. Laying on top of her, Conan ground his half hard cock between Gwendolyn’s legs, fingers tiptoeing down her abdomen while their tongues wove together, when suddenly Conan froze and pulled back.

“Holy shit, honey,” he studied her face. “When was the last time I made you cum?”

Eyes shifting, Gwendolyn smiled sheepishly. “Well, it’s been a few days…”

“Gwen, I’m so sorry. Fuck. I can’t believe I’ve been so selfish.” Closing his eyes, he shook his head.

“Oh honey, it’s fine.” Gwendolyn scratched his beard. “I know how exhausted you’ve been. Really, don’t worry about it.”

Conan pressed a kiss to her collarbone. “Well, I guess I’ll just have to make up for it now.” Grinning mischievously, he caught her lips again and his fingers parted her, twirling around her clit until she was slick and anxious. Lowering himself a little, Conan inserted three lengthy freckled fingers inside of her, locating her g-spot expertly while his thumb rotated over her swollen nub. 

“ _ Conan, yes! Fuck! _ ” Gwendolyn clung to his shoulders, mouth agape as she rutted against his hand.

“Does that feel good?” Conan whispered into her skin as he kissed her neck. “Am I going to make you cum? Huh?”

Her hands scrambled frantically against his back as Gwendolyn writhed up and down on the mattress. “ _ Oh Conan! Yes! YES! _ ” Fluttering around his fingers, Conan withdrew and sucked them into his mouth, reveling in her sweet taste. He drew patterns on her stomach as he waited for her to come down, then he laid on his back and reached over to smack Gwendolyn’s ass.

“Come on babe, you’re gonna ride my face.” He grinned.

“What?”

“Yup.” Conan made his eyebrows dance, patting his own cheek. “Hop on.” 

“But…” Gwendolyn looked at Conan, then down at herself. “Won’t I be too heavy?”

Shaking his head, Conan waved a hand. “Nah, it’ll be fine. Tell you what, if I’m having any trouble, I’ll pinch your ass twice. Like this.” He demonstrated and Gwendolyn squeaked, which made him laugh.

“Okay then.” Gwendolyn said hesitantly. Placing one leg on either side of Conan’s head, she held onto the top of the headboard and kept most of her weight aloft as she positioned herself over Conan’s mouth. But his arms, wiry with muscle, came up and clamped around her hips, dragging her down until his sharp jaw dug into her and Conan’s tongue was rotating around her clit with tremendous pressure.

“Oh,  _ oh, that’s… _ ” Body curving forward, Gwendolyn’s breath grew shallow as one hand gripped the headboard until her knuckles were white, the other fisting into Conan’s orange hair. His thin lips locked around her clit, gravity making the suction incredible and soon she was humping his face without shame and screaming, “ _ Oh Conan! Oh fuck! I’m cumming! I’m cumming! _ ” Again and again as the orgasms rolled into one another almost seamlessly. Thighs locked around his head, Gwendolyn wasn’t sure how he could breath, but Conan didn’t seem perturbed, moaning into her and jerking his hard cock with a free hand as the sounds of her ecstasy aroused him. Quaking above him, Gwendolyn’s screams sounded like sobs as the storm broke once again, electricity passing over her flesh, vision going black for a moment, sounds hazy until everything came rushing back with a gasp.

Falling to the side, Gwendolyn curled in on herself, hand to her chest, gulping air through the fabric of the pillow.

Conan wiped his face and stroked her arm. “You okay?”

Barely able to nod, Gwendolyn lifted three fingers in what she hoped Conan would take as a positive response. Conan played with her sweaty hair while reality shifted back into place around her. After a few minutes Gwendolyn shifted and met Conan”s eyes. 

“That...was amazing.” She breathed.

Smirking, Conan trailed his fingers down her side. “I’m glad you liked it.” Getting close to her face, he drew his nose across her cheek. “You want me to fuck you now?” 

“Yes.” Gwendolyn tossed a leg over his hip and Conan rolled on top of her. Dragging the head of his cock over her entrance, their eyes met for a moment and he looked at her questioningly, Gwendolyn giving him a little nod. Tipping forward, Conan exhaled in relief as her body surrounded him. Beginning to roll his hips, Conan worked his fingers over Gwendolyn’s clit at the same time, but he was so worked up from the sounds she made while sitting on his face that he he grabbed one of her legs and threw it over his shoulder, pounding into her recklessly until the headboard hammered against the wall.

“ _ Conan! Fuck! FUCK! _ ” Screaming, her nails dug canals into his back but it didn’t stop him, Conan rocketed forth, tucking his head into the crook of Gwendolyn’s neck after she clenched around him the second time.

“ _ Oh Gwen! Yes! Fuck! Gwen! _ ” A stuttering whine rose from his throat as every muscle in his body strained before Conan shot into her, only for them to become a useless puddle of limbs.

Untangling themselves, Conan sat up and Gwendolyn combed the sweaty hair out of her face.

“Well, that was…” Gwendolyn brought a hand to her neck, when she spoke her voice sounded froggy. “Oh, my throat hurts from screaming I think.” They both laughed.

“Yeah, well, you’ve never been exactly quiet.” Conan scratched the back of his head, grinning.

Gwendolyn kicked him playfully. “And whose fault is that? Oh shit…” she glanced around the room. “Who are we sharing walls with?”

“Um…” Conan gathered his eyebrows in thought, pointing at the wall in front of them. “Well, that’s Sona I think. But she’s always watching Netflix with headphones in, and she wears earplugs to sleep, so we might be okay there. But, uh…” Conan gestured behind him with a thumb and started to laugh. “Bley is on the other side.” Hands on his belly, Conan threw back his head, rolling with mirth. “He’s...he’s not going to be able to look you in the face for a  _ month. _ ” Gwendolyn joined in, and they spent the rest of their day off in bed, ordering room service, napping, and enjoying a day without interruption.

***

After settling in Reno, they were all hanging out in the common area of the hotel, when Gwendolyn was on her way back from the gift shop and coming around the corner, ran into Aaron Bleyaert.

“Oops, sorry Bley.” Gwendolyn delicately placed a hand on his shoulder as she walked into the room with the others.

Eyes shifting away from her, two pink spots rose on Bley’s cheeks and he nodded. “No...no problem. Gwen. Bye.” He scurried away and Conan burst out laughing as Gwendolyn joined him on the couch.

“Aw, don’t laugh.” Gwendolyn nudged his shoulder. “He’s obviously so uncomfortable.”

Conan shook his head. “Oh, come on. It’s funny. Tell you what.” He crooked a finger to draw Gwendolyn in conspiratorially. “Why don’t we mess with him a little?”

When Bley returned, Gwendolyn was sitting at a table with her laptop, eyes furrowed in concentration. “Hey Bley?” She called out. “I’m trying to set up a video chat with a friend of mine, but I’m having trouble. Could you help me out?”

“Oh, um...yeah. Sure.” He bobbed his silver hair and made his way over. Gwendolyn stood and gestured for Bley to take her chair. Typing away for a few minutes, Bley peered at the screen where Gwendolyn’s friend Missy’s face was hovering.

“I, um...it should be working…” he waved a hand in front of the camera lens. “Hello?” Gwendolyn had texted Missy in advance and told her to act as though the chat was defective. 

Looking down at her phone with mock concern, Gwendolyn shook her head. “She just texted me and said she can’t see or hear us.” Gathering her hair over one shoulder, Gwendolyn bent from the waist and leaned forward so her cleavage would be directly in Bley’s line of sight as she appeared to study the screen. Watching as Bley tried not to look, got flustered, and turned pink, Conan had to cover his mouth to keep from laughing.

“Do you have any idea what the problem might be?” Gwendolyn leaned her arm on Bley’s shoulder and he blinked rapidly, shifting in the chair.

“I, um…” he cleared his throat. “I can try a couple of other things.” Fingers flying over the keyboard, Conan noticed his eyes trailed for half a second down her dress, but Bley hastily corrected himself. “There, uh...can you see us now?” He waved again. Texting Missy to drop the act, she responded on the screen and Gwendolyn clapped a little.

“Thank you, Bley.” Smiling at him, Gwendolyn carded her fingers through his gray hair and Bley’s eyes went wide with shock. “You’re so helpful…” Sliding onto his lap, Gwendolyn draped her arms around his shoulders and Bley froze, raising his hands like a criminal cornered by the police and turned to face Conan.

“I...I…”

The room roared with laughter. Bley’s eyes shifted around, confused. 

“Sorry, Bley.” Gwendolyn kissed him on the cheek before standing up, and if possible he turned a deeper shade of pink. “We just wanted to have some fun with you.” As per usual, Bley was a good sport about it and took it in stride.

The show at The Grand that night went smoothly, and as they piled in the plane to head to San Jose, Conan and Gwendolyn snuggled up next to each other, falling asleep somewhere over state lines.


	4. 4

Watching from the wings of the Macky Auditorium, Gwendolyn smiled as Conan charged into the crowd, guitar slung over his shoulder, arms aloft. She always found it slightly amusing that a horde of people paid for a meet and greet before the show, only for Conan to get irrationally high on the energy of the crowd and rush forward to hug anyone who would have him for free.

Losing sight of his iconic orange hair for a moment, Gwendolyn’s eyes scanned the sea of people, and when she still couldn’t see him after a minute she began to grow concerned.

Then Conan appeared. No idea how he managed it, Gwendolyn spotted Conan high on the left balcony, foot balanced on the railing, arms held above his head as the audience roared their approval. Gwendolyn’s heart stopped.  _ Jesus fucking Christ _ . All it would take is one overzealous fan, one small push…

But Conan stepped down, disappearing back into the fray and reemerging a moment or two later on the ground level, jogging back up to the stage to resume the show. Closing things with a bang, Gwendolyn was fuming when Conan strode off with a crazed smile.

“Hey, honey, how’s it—“

Grabbing Conan by the collar of his shirt, Gwendolyn brought her face close. “What the hell is  _ wrong  _ with you?”

“What?” Covering her hands with his own, Conan narrowed his baby blue eyes in confusion and took a step back.

Gwendolyn released one hand and gestured to the auditorium. “What the fuck was that on the balcony? Do you have some kind of death wish or something?”

“Aw, come on, Gwen.” Conan chuckled. “I was just having a little fun.”

“Well, I didn’t think it was funny.” Shaking her head, Gwendolyn shut her eyes and brought a hand to her face. “If something happened to you, Conan, I...I wouldn’t…” She let out a long, slow breath.

“Oh, oh, come here…” Conan wrapped his lanky arms around her, pressing a kiss to the top of her head. “I’m sorry I made you worry.” He spoke into her crimson hair.

Nodding, Gwendolyn wrapped her arms around his slender frame. “Just...just don’t do that again, okay?”

“I won’t.” Rubbing her back, they parted and made their way to the hotel.

***

The second show in Colorado went well, and they packed up after to make their way to Boston for Conan’s 25 year college reunion. Plane setting down in Massachusetts, Gwendolyn shifted nervously in her seat. While they were in town, Conan suggested they stop by his parent’s house for lunch. It would be her first time meeting them and Gwendolyn was more than a little apprehensive.

Arriving at the suburban home, Gwendolyn got out of the car and wiped her hands on her dress.

“You okay?” Conan put his arm around her shoulder.

Gwendolyn nodded, smiling. “Yeah, yeah. Just nervous.”

“You’ve got nothing to worry about. They’re gonna love you.” He kissed the top of her head and walked through the front door without knocking.

“Mom? Dad?” Conan called into the house. A short, squat woman with bone structure resembling Conan’s came out of the kitchen, wiping her hands on a dish towel.

“Hello Pigeon Pie.” She said cheerily. Conan bent down to hug her and she patted his cheek. “And you must be Gwen, I’m Ruth, Conan’s mother.” Extending a hand, Gwendolyn shook it politely.

“Hello Ruth, nice to meet you. You have a lovely home.” Gwendolyn peered around, smiling. Just then a tall man appeared who looked so similar to how Conan would look in 25 years it caused Gwendolyn’s mind to flash forward to their life together unbidden, forcing her to shake her head to get back to the present. 

Ruth gestured over her shoulder. “And this is my husband, Tom.” He raised a hand in acknowledgement and Gwendolyn grinned. “Lunch is just about ready if you want to sit down.”

“Do you need any help in the kitchen?” Gwendolyn offered.

Smiling, Ruth nodded. “That would be lovely, dear. Thank you.” Giving Gwendolyn the job of mashing the potatoes, they made pleasant small talk about what books they were reading. Then following a brief pause Ruth looked up from the roasted chicken she finished tenting with foil and tilted her head. “You know, Conan is very taken with you.”

“Oh yeah?” Gwendolyn raised an eyebrow, smiling as she added more garlic salt to the potatoes.

Ruth nodded. “Yes. I don’t think I’ve ever seen him this way about another girl before.” 

Blushing, Gwendolyn helped Ruth carry the dishes to the table, and altogether it was a lovely meal. At one point, however, Ruth did feel the need to chide Conan about his beard.

“Don’t you think it’s time you shaved it off, dear?”

Conan sighed. “I like it, mom.”

“But Conan, it makes you look...homeless.” They all burst out laughing and Conan scratched at the deep red scruff.

“Don’t worry, mom. I haven’t started my new job yet, but I don’t think there’s a chance of that happening anytime soon.”

When they finished, Ruth hugged Gwendolyn and they made their goodbyes before heading out to the car and going back to the hotel.

As they drove, Conan squeezed her thigh. “See? Now that wasn’t so bad, was it?”

“Yeah.” She nodded. “They’re really nice.”

“What, did you think I was raised by wolves?” He smirked.

Gwendolyn scratched under his chin. “Well, you can get pretty wild, after all.”

Conan smiled. “You don’t secretly want me to shave the beard, do you?”

“Oh god no.” Gwendolyn shook her head. “I love it. Super sexy. Even if it does mean my thighs are chafed half the time.”

Chuckling wickedly, Conan pulled into the hotel parking lot. Changing, they met with the rest of the crew and made their way to the Harvard campus. Conan looked especially handsome in a blue shirt that made his eyes dazzle while they waited for their turn to hit the stage. Gwendolyn wasn’t sure who was in charge of the event, but whoever it was she couldn’t imagine why they thought a group of adults approaching 50 putting on a talent show was a good idea. Though she of course loved watching Conan and the band perform, watching the other acts on a television was cringe-worthy as mimes and the like plied their wares before former school mates.

Plucking out some of their favorite tunes in the downtime with Jimmy and the guys, Gwendolyn watched Conan with admiration until it was time for him to take the stage. They played  _ Rock This Town _ by The Stray Cats and Gwendolyn was once again struck by how Conan was able to push his voice into such raw, powerful realms as his fingers expertly danced over the strings and he moved across the stage. When they finished, she heard a lot of people whispering in impressed voices about how they had no idea Conan could sing or play guitar, and she smiled in secret pride.

Later that night on their way to Dallas, the cabin of the plane was dark and silent except for a couple of soft snores. Everyone was exhausted from the day’s events, but Gwendolyn found she couldn’t sleep. Sitting next to her, Conan was scrolling absently through his phone. Gwendolyn sat up in her chair and looked around. Not seeing any open eyes, she leaned over and began pressing kisses to Conan’s neck, her fingers tiptoeing across his thigh under the blanket they shared.

Chuckling a little, Conan let the arm holding his phone fall by his side and turned to her. “What do you think you’re doing?” He asked softly.

Gwendolyn brought her lips to his ear as her hand slid over the bundle of his crotch. “C’mon. Everyone’s asleep.” 

Shaking his head, Conan smiled, then looked around cautiously before hiking the blanket up higher. Gwendolyn felt his long fingers working up the inside of her thigh as she undid his zipper and slipped inside. Catching her mouth, Conan’s hand made its way below the waistband of her panties, not bothering with any pretext, but rubbing her clit hard and fast. Knowing the flight attendant could come through for a cabin check at any moment, Gwendolyn did the same. Gripping his cock and tugging furiously under the blanket until they were both panting into one another’s open mouths. 

Gwendolyn rocked into Conan’s freckled hand subtly, and it was a matter of minutes before his fiddling fingers pushed her over the edge, nails digging into her armrest and clenching her teeth to maintain silence. 

When her shivering subsided, Conan withdrew his hand, sucking the fingers into his mouth. Gwendolyn doubled her efforts around his cock, kissing and nipping at his neck as he pressed his head back into the seat and ground his heels into the floor. After a couple of minutes Conan’s eyes opened and he tapped her arm in a panic. With a quick peek around, Gwendolyn ducked under the blanket and sank her mouth over his thick cock, sucking hard as Conan thrust into her throat, hot cum trickling down the back of her tongue. 

Surfacing, Gwendolyn was still pushing her hair out of her face when the door to the cockpit opened and the flight attendant peeked out to make sure everything was in order. When she disappeared, Conan and Gwendolyn couldn’t help breaking out in a fit of quiet giggles.

***

The rest of the shows in May went by in a flash of meet and greets, sound checks, and exhausted flights. Gwendolyn noticed Conan growing skinnier with every city they stopped in, and she did what she could to ply him with food every chance she got, keeping a baggie of cheese popcorn on herself at all times whenever she could convince him to have a snack.

Finally it came time for the big show at Radio City in New York. On the flight out, Gwendolyn sensed a tension in Conan as he sat next to her. Going to Radio City, so near where he filmed Late Night for all those years, held a tremendous weight for him that was hard to describe, and Gwendolyn knew that even though this was a venue he ached to play, there was a bittersweetness on that street.

Not long before the first show, Gwendolyn looked on as Conan joked around with Stephen Colbert and Jon Stewart. Seeing him loose and happy with his friends was a relief, and when Paul Rudd and Bill Hader joined they reached new heights of ridiculous. As usual, Conan introduced her to the guys and Gwendolyn wasn’t surprised to find them all friendly and kind.

The show was a blowout, and after Conan was buzzing with the high of the crowd, insisting on going outside to sign autographs for the better part of an hour before the tour manager Gus finally managed to drag him into a waiting van.

Back at the hotel, Conan recounted the show to Gwendolyn as though she hadn’t been watching from the wings, and she just smiled as he paced back and forth across the room, gesturing wildly with his hands.

“And then, and then these panties fly on stage, right?” Conan turned toward her, but he didn’t seem to see Gwendolyn, too lost in his reminiscence . “And this isn’t the first time, of course, so I picked them up and started you know,” Conan spun his finger in the air. “Twirling them around. And then this woman about three rows back.” Conan chuckled and ran a hand over his face. “She makes a megaphone with her hands.” Conan proceeded to demonstrate for Gwendolyn’s benefit. “And she yells at me, ‘ _ No! Those are for Bill!’. _ ” Finally collapsing into a chair, Conan clutches his belly, throwing his head back and laughing.

Gwendolyn chuckled. “Well, can’t blame her there.” She shrugged.

“Excuse me?” Conan leaned forward, elbows on his knees and folding his hands. “What was that?”

Realizing what she’d said, Gwendolyn’s eyes went wide for a moment before shifting away. “Oh, um…” she swallowed.

A slow smirk spread across Conan’s face. “Are you telling me you think Bill is  _ attractive _ ?”

Blushing, Gwendolyn bit her lip and covered her eyes. “I plead the fifth and refuse to answer on the grounds that my response may tend to incriminate me.”

“Well,” Conan sat back in the chair, nodding and smacking the arms with his hands. “Bill and I had a good run. That friendship is over.” They both laughed and crawled into bed, Conan’s energy raring down enough to allow him to sleep.

***

Once they hit Nashville, Conan decided to add a secret show for his fans at Jack White’s Third Man Records studio. Packed to the rafters and boiling, even in a spaghetti strap dress Gwendolyn’s hair was sticking to her face and a trickle of sweat fell down her back. But that was nothing compared to Conan. Jumping around on stage, his black button up was plastered to his flesh, sweat springing from him with every movement. 

Panting as he walked toward her, Gwendolyn handed him a bottle of water that he drained and immediately handed him another. Peeling the shirt from his skinny frame, Conan bunched it up and rang it out.

“Gross.” He chuckled as sweat poured onto the floor. Gwendolyn knew she should probably be disgusted, but there was something about Conan standing there, chest heaving, hair wet against his head, rivulets of sweat trickling down his muscled abdomen, that got her excited. Shaking the damp shirt loose, he draped it over his shoulders unbuttoned and they went outside where it was barely cooler before climbing in the van and heading to the hotel.

“Shower,  _ please. _ ” Conan groaned once they peeled themselves off the leather seats and made it up to their room. Gwendolyn turned the water on as cold as it would go and they left their clothes in a soggy pile on the hotel room floor, stepping under the chilly stream and sighing with relief.

“Fuck that feels amazing.” Conan leaned his head back under the showerhead, eyes closed in reverie.

Gwendolyn playfully smacked his shoulder. “Hey, you’re hogging it, no fair. It’s my turn.”

“Oh yeah?” Conan opened his eyes, smirking. Tipping forward, his hand cupped Gwendolyn’s ass. “And why should I be fair?”

Smiling, Gwendolyn caught his mouth and she could still taste the saltiness of his sweat as Conan pushed her against the shower wall. Hooking his hands under her thighs, Conan lifted her and Gwendolyn wrapped her legs around his waist. Despite how thin he looked, Conan was wiry steel and he had no trouble holding her aloft as he ground himself between her legs.

“You want me to fuck you? Huh?” Conan kissed his way down the wet flesh of her neck while Gwendolyn clung to his shoulders.

Breath warm against his ear, Gwendolyn rutted her hips against him. “Yes. Fuck me, Conan.” Rubbing the head of his cock between her lips a few times, Conan surged forward with a groan, keeping her up with one hand, the other playing over her clit as their tongues danced together.

Conan swiveled into her, Gwendolyn squeaking up and down the shower wall as water cascaded over them. 

“ _ Oh Conan! Yes! Fuck! _ ” Gwendolyn moaned, circle of her legs tightening to draw him near. Conan could feel her fluttering around his cock and he began pounding into her recklessly, Gwendolyn’s thigh quaking in his grip.

“ _ Gwen! Fuck! Yeah! Gwen! _ ” She seized around him at the precise moment when his hips lost control and shot forth into her for the last time, fingertips digging into soaked flesh as they cried one another’s names. 

Conan let her down and Gwendolyn had to hang onto his shoulder for a moment while her legs steadied themselves beneath her. Chuckling, Conan brushed a kiss to her dewy forehead. “You’re so beautiful, you know that?”

Gwendolyn scratched his soggy beard. “Thank you, handsome.” They proceeded to go about the business of washing themselves before toweling off, refreshed and satisfied.

Bonnaroo. Tens of thousands of people. Dozens of musicians. 90+ degree heat. Conan was scheduled not only to perform, but to announce some of the acts. One problem, no one told him until the day of that they were expecting Conan to come up with schtick for every one of the artists he had to precede. Aggravated at yet another wrench thrown in at this late stage in the tour, Gwendolyn massaged Conan’s shoulders while he worked on material with Andy, Mike, and the others.

Already hot and stressed, Gwendolyn couldn’t believe it when they told her the tent in which Conan and the band would be performing had lost air conditioning. She watched in horror as her poor, beloved Conan insisted on strutting out in his pink paisley Raw pleather suit despite the immense heat. As the fans cheered, she wondered if they truly appreciated all the sacrifices Conan went through to make sure they had a spectacular show.

Afterward, Conan managed to find one duct pumping in air conditioning and stood before it with his head down, shirtless and eyes closed. Tentatively walking up to him, Gwendolyn didn’t want to touch him and risk transferring any additional body heat, so she leaned against the equipment and spoke softly.

”Hey honey, how are you holding up?”

Conan let out a long, slow sigh. “I’m...I don’t even know. Exhausted doesn’t cover it.” Turning around, he laid his head back to get a different angle on the incoming draft. 

“I’m sorry, Conan. I know how hard you’re working. Do you need anything?” She tilted her head in concern.

Smiling weakly, Conan shook his head. “No babe, thank you though. You’ve been so great through all of this.” Gwendolyn grinned and Conan peeled himself away from the AC.

The second day at Bonnaroo went much as the first. Just as hot, just as hectic, but when they were done and winging their way to Georgia, everyone found themselves suddenly wistful as the last show rose over the horizon

Conan and the gang pulled out all the stops for their final performance, giving the audience a night they would never forget. When Conan walked offstage, Gwendolyn took his face in both hands. “I am  _ so damn proud  _ of you.” She smiled, kissing him deeply.

”Thanks, honey.” Conan pushed an errant strand of red hair back from her face. “Thank you so much for coming with me. Having you here it...it made all the difference.”

“Of course.” Gwendolyn polished one of his prominent cheekbones. The night was filled with tearful goodbyes and thank you’s as they wrapped up, Conan hugging Sona and telling her she should be proud of herself, thanking Andy for coming along, and genuinely expressing how grateful he was to everyone involved for allowing him to live out his dream of touring and getting a taste of being a rockstar.

Finally flying back to Los Angeles, Conan squeezed Gwendolyn’s hand. “Well, ten weeks. It went by faster than I thought it would.”

Gwendolyn nodded. “Yeah, and we managed not to kill each other, so that’s something.” She chuckled.

“Yeah, about that…” Conan shifted in his seat to face her. “I was thinking, why don’t, um...why don’t you move in? You know, when we get back.”

A smile spread across Gwendolyn’s face. “Really?”

“Yeah.” Conan nodded. “I think we’re ready, don’t you?”

Grinning, Gwendolyn reached up to comb her fingers through Conan’s orange hair. “Yes. I do.”

  
  
  
  
  


THE END

**Notes for the Chapter:**

> Thank you for taking the time to read! If you enjoyed this story, please leave a comment or come say hi on tumblr at fandomtransmandom


End file.
